Pravadoline - CAS 92623-83-1
Category: Inhibitor
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Pravadoline is a COX inhibitor and cannabinoid CB agonist used as an anti-inflammatory and analgesic agent. It inhibits prostaglandin synthesis, and it also suppresses neuronally stimulated contractions in mouse model, which differs from NSAIDs.
Brife Description:
COX inhibitor
anti-inflammatory and analgesic agent
Canonical SMILES:
1.Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor.
D'Ambra TE;Estep KG;Bell MR;Eissenstat MA;Josef KA;Ward SJ;Haycock DA;Baizman ER;Casiano FM;Beglin NC J Med Chem. 1992 Jan;35(1):124-35.
Pravadoline (1) is an (aminoalkyl)indole analgesic agent which is an inhibitor of cyclooxygenase and, in contrast to other NSAIDs, inhibits neuronally stimulated contractions in mouse vas deferens (MVD) preparations (IC50 = 0.45 microM). A number of conformationally restrained heterocyclic analogues of pravadoline were synthesized in which the morpholinoethyl side chain was tethered to the indole nucleus. Restraining the morpholine diminished the ability of these pravadoline analogues to inhibit prostaglandin synthesis in vitro. In contrast, mouse vas deferens inhibitory activity was enhanced in [2,3-dihydro-5-methyl-3-[(4-morpholinyl)methyl] pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-(4-methoxyphenyl)methano ne (20). Only the R enantiomer of 20 was active (IC50 = 0.044 microM). An optimal orientation of the morpholine nitrogen for MVD inhibitory activity within the analogues studied was in the lower right quadrant, below the plane defined by the indole ring. A subseries of analogues of 20 and a radioligand of the most potent analogue, (R)-(+)-[2,3-dihydro-5-methyl-3-[(4-morpholinyl)methyl]pyrrolo [1,2,3-de]-1,4-benzoxazin-6-yl](1-naphthalenyl)methanone (21) were prepared. Inhibition of radioligand binding in rat cerebellar membranes was observed to correlate with functional activity in mouse vas deferens preparations.
2.Combined antiproliferative effects of the aminoalkylindole WIN55,212-2 and radiation in breast cancer cells.
Emery SM;Alotaibi MR;Tao Q;Selley DE;Lichtman AH;Gewirtz DA J Pharmacol Exp Ther. 2014 Feb;348(2):293-302. doi: 10.1124/jpet.113.205120. Epub 2013 Nov 20.
The potential antitumor activity of cannabinoid receptor agonists, such as the aminoalklylindole WIN55,212-2 (WIN2), has been studied extensively, but their potential interaction with conventional cancer therapies, such as radiation, remains unknown. In the present work, the influence of WIN2 on the antiproliferative activity of radiation in human (MCF-7 and MDA-MB231) and murine (4T1) breast cancer cells was investigated. The antiproliferative effects produced by combination of WIN2 and radiation were more effective than either agent alone. The stereoisomer of WIN2, WIN55,212-3 (WIN3), failed to inhibit growth or potentiate the growth-inhibitory effects of radiation, indicative of stereospecificity. Two other aminoalkylindoles, pravadoline and JWH-015 [(2-methyl-1-propyl-1H-indol-3-yl)-1-naphthalenyl-methanone], also enhanced the antiproliferative effects of radiation, but other synthetic cannabinoids (i.e., nabilone, CP55,940 [(+)-rel-5-(1,1-dimethylheptyl)-2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-phenol], and methanandamide) or phytocannabinoids [i.e., Δ⁹-tetrahydrocannabinol (THC) and cannabidiol] did not. The combination treatment of WIN2 + radiation promoted both autophagy and senescence but not apoptosis or necrosis.
3.Pravadoline: profile in isolated tissue preparations.
Ward SJ;Mastriani D;Casiano F;Arnold R J Pharmacol Exp Ther. 1990 Dec;255(3):1230-9.
Pravadoline is a novel cyclooxygenase-inhibiting analgesic with a preclinical profile of activity in vivo clearly distinct from that of other cyclooxygenase inhibitors. The purpose of the present study was to assess the possibility that pravadoline possesses pharmacologic actions in addition to inhibition of cyclooxygenase. The data demonstrate that pravadoline inhibits neuronally stimulated contractions of the guinea pig ileum and mouse vas deferens preparations. These actions of pravadoline are not shared by known cyclooxygenase inhibitors, but are mimicked by close structural analogs of pravadoline devoid of the ability to inhibit prostaglandin formation. Some structural analogs were inhibitory also in the rat vas deferens preparation. The inhibitory effects of pravadoline and a representative noncyclooxygenase-inhibiting analog in isolated tissue preparations are not mediated by an interaction with muscarinic cholinergic, adrenergic (alpha-1 or alpha-2), serotonin (5-hydroxytryptamine2 or 5-hydroxytryptamine3), opioid (mu, kappa or delta), purinergic (P1), neurokinin-1, bradykinin (B2) or prostaglandin (E2) receptors. It is concluded that pravadoline and aminoalkylinodole analogs are inhibitory in several bioassay systems via a presynaptic mechanism which does not involve inhibition of cyclooxygenase, or the activation or inhibition of several known receptors.
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CAS 92623-83-1 Pravadoline

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